Abstract
l-Carnitine, a quaternary ammonium compound, plays an important role in Β-oxidation of fatty acids in mammals. The increasing demand for this compound in medicine has led to the development of numerous procedures for l-carnitine production. This review discusses the possibilities of microbial and enzymatical synthesis of l-carnitine and gives an overview on the pathways of l-carnitine metabolism and related enzymes in microorganisms.
This is a preview of subscription content, log in via an institution.
Preview
Unable to display preview. Download preview PDF.
References
Bremer J (1983) Physiol Rev 63: 1420
Gulewitsch W, Krimberg R (1905) Hoppe-Seyler's Z Physiol Chem 45: 326
Kutscher FZ (1905) Untersuch Nahr Genussm 10: 528
Tomita M, Sendju Y (1927) Hoppe-Seyler's Z Physiol Chem 169: 263
Friedman S, Fraenkel GS (1972) Carnitine. In: Sebrell WH, Harris RS (eds) The vitamins, 2nd edn. Academic Press, New York, vol 5, p 329
Fritz IB (1963) Adv Lipid Res 1: 285
Bieber LL (1988) Ann Rev Biochem 57: 261
Borum PR (1983) Ann Rev Nutr 3: 233
Scholte HR, de Jonge PC (1987) Metabolism, function and transport of carnitine in health and disease. In: Gitzelmann R, Baerlocher K, Steinman B (eds) Carnitin in der Medizin. Schattauer, Stuttgart, p 21
Tanphaichitr V, Broquist HP (1973) J Biol Chem 248: 2176
Wolf G, Berger CRA (1961) Arch Biochem Biophys 92: 360
Rebouche CJ, Broquist HP (1976) J Bacteriol 126: 1207
Borum PR, Broquist HP (1977) J Biol Chem 252: 5651
Paik WK, Kim S (1975) Adv Enzymol Relat Areas Mol Biol 42: 227
Henderson LM, Nelson PJ, Henderson L (1982) Fed Proc 41: 2843
Rebouche CJ, Engel AG (1980) Biochim Biophys Acta 630: 22
Bremer J (1962) Biochim Biophys Acta 57: 327
Lindstedt G, Lindstedt S (1970) J Biol Chem 245: 4178
Rebouche CJ, Engel AG (1980) J Biol Chem 255: 8700
Engel AG, Angelini C (1973) Science 179: 899
Carroll EC, Carter AL, Perlman S (1987) J Nutr 117: 1501
Gilbert EF (1985) Pathology 17: 161
Rebouche CJ, Paulson DJ (1986) Ann Rev Nutr 6: 41
Hulsmann WC (1991) Cardiovascular Drugs and Therapy 5: 7
Meier PJ (1987) d-Carnitin, harmlos? In: Gitzelmann R, Baerlocher K, Steinman B (eds) Carnitin in der Medizin. Schattauer, Stuttgart p 101
Emaus KR, Bieber LL (1983) J Biol Chem 258: 13160
Kleber HP, Claus R (1982) DD 204 378
Kleber HP, Claus R (1981) DD 211 039
Kleber HP, Claus R, Seim H, Strack E (1981) DD 204 105
Typelt H, Claus R, Nitzsche K (1991) J Biotechnol 18: 173
Strack E, Lorenz I (1960) Hoppe-Seyler's Z Physiol Chem 318: 129
Strack E, Müller DM (1972) Hoppe-Seyler's Z Physiol Chem 353: 618
Cavazza C (1980) Germ Offen DE 2927672
Comber RN, Brouillette WJ (1987) J Biol Chem 52: 2311
Voeffray R, Perlberger JC, Tenud L, Gosteli J (1987) Helv Chim Acta 70: 2058
Bock K, Lundt I, Pederson C (1983) Acta Chem Scand, Ser B 37: 341
Fiorini M, Valentini C (1982) Eur Patent Appl EP 60595
Zhou B, Gopalan AS, Van Middlesworth F, Shieh WR, Sih CJ (1983) J Am Chem Soc 105: 5925
Seebach D, Giovannini F, Lamatsch B (1985) Helv Chim Acta 68: 958
Renaud P, Seebach D (1986) Synthesis 5: 424
Bellamy FD, Bondoux M, Dodey P (1990) Tetrahedron Lett 31: 7323
Kleber HP, Seim H, Aurich H, Strack H (1977) Arch Microbiol 112: 201
Miura-Fraboni J, Englard S (1983) FEMS Microbiol Lett 18: 113
Miura-Fraboni J, Kleber HP, Englard S (1982) Arch Microbiol 133: 217
Seim H, Löster H, Claus R, Kleber HP, Strack E (1982) FEMS Microbiol Lett 15: 165
Kleber HP (1991) Metabolism of trimethylammonium compounds by Acinetobacter. In: Towner KJ, Bergogne-Berezin E, Fewson CA (eds) The Biology of Acinetobacter. Plenum, New York, p 403
Sih CJ (1985) WO Patent Appl 85/04900
Sih CJ (1988) US Patent Appl US 4751 182
Aragozzini F, Manzoni M, Cavazzoni V, Craveri R (1986) Biotechnol Lett 8: 95
Kawamura M, Akutsu S, Fukuda H, Hata H, Morishita T, Kano K, Nishimori H (1987) Jpn Kokai Tokkyo Koho JP 62, 118, 899
Dropsy EP, Klibanov AM (1984) Biotechnol Bioeng 26: 911
Francalanci F, Ricci M, Cesti P, Venturello C (1987) Eur Patent Appl EP 237 983
Bianchi D, Cabri W, Cesti P, Francalanci F, Ricci M (1988) J Org Chem 53: 104
Patel SS, Conlon HD, Walt DR (1986) J Org Chem 51: 2842
Bremer J (1962) J Biol Chem 237: 228
Fritz IB, Schultz SK, Srere PA (1963) J Biol Chem 238: 2509
Chase JFA, Pearson DJ, Tubbs PK (1965) Biochim Biophys Acta 96: 162
Marquis NR, Fritz IB (1965) J Biol Chem 240: 2197
Colucci WJ, Gandour RD (1988) Bioorg Chem 16: 307
Kawamoto S, Ueda M, Nozaki C, Yamamura M, Tanaka A, Fukui S (1978) FEBS Lett 96: 37
Ratledge C, Gilbert SC (1985) FEMS Microbiol Lett 27: 273
Ueda M, Tanaka A, Fukui S (1982) Eur J Biochem 124: 205
Claus R, KÄppeli O, Fiechter A (1982) Anal Biochem 127: 376
Kispal G, Cseko J, Alkonyi I, Sandor A (1991) Biochim Biophys Acta 1085: 217
Ueda M, Tanaka A, Fukui S (1984) Eur J Biochem 138: 445
Miyazawa S, Ozasa H, Furuta S, Osumi T, Hashimoto T (1983) J Biochem 93: 439
Kozulic B, KÄppeli O, Meussdoerffer F, Fiechter A (1987) Eur J Biochem 168: 245
Mittal B, Kurup CKR (1980) Biochim Biophys Acta 619: 90
Markwell MAK, Tolbert NE, Bieber LL (1976) Arch Biochem Biophys 176: 479
Chase JFA (1967) Biochem J 104: 1503
McCreary MD, Lewis DW, Wernick DL, Whitesides G (1974) J Am Chem Soc 96: 1038
Ouyang T, Walt DR (1991) J Org Chem 56: 3752
Nakayama K, Haruo H, Ogawa Y, Ozawa T, Ota T (1989) Jpn Kokai Tokkyo JP 01222 796
Nakayama K, Honda H, Ogawa Y, Ozawa T, Tetsuo O (1989) Jpn Kokai Tokkyo JP 01 222 797
Nakayama K, Honda H, Ogawa Y, Ozawa T, Ota T (1988) Germ Offen DE 3 728 321
Nakayama K, Ota T (1989) Jpn Kokai Tokkyo JP 01 213 258
Nakayama K, Ota T (1989) Jpn Kokai Tokkyo JP 01 213 259
Nakayama K, Yuki O, Honda H, Okta T, Ozawa T (1989) Eur Patent Appl EP 319 344
Jung K, Kleber HP (1984) Wiss Z Karl-Marx-Univ Leipzig, Math-Naturwiss R 34: 293
Aurich H, Kleber HP, Sorger H, Tauchert H (1968) Eur J Biochem 6: 196
Aurich H, Kleber HP, Schöpp W (1967) Biochim Biophys Acta 139: 505
Kleber HP, Seim H, Aurich H, Strack E (1978) Arch Microbiol 116: 213
Goulas P (1988) Biochim Biophys Acta 957: 335
Mori N, Kasugai T, Kitamato Y, Ichikawa Y (1988) Agric Biol Chem 52: 249
Takahashi M, Nagasawa S, Matsuura K (1991) Ger Offen DE 4 032 287
Mori N, Shirota K, Kitamoto Y, Ichikawa Y (1988) Agric Biol Chem 52: 851
Schöpp W, Sorger H, Kleber HP, Aurich H (1969) Eur J Biochem 10: 56
Vandecasteele JP, Lemal J (1980) US Patent Appl US 4221 869
Vandecasteele JP (1980) Appl Environm Microbiol 39: 327
Vandecasteele JP, Ballerini D, Lemal J, Le Penru Y (1985) US Patent Appl US 4 542 098
Souppe J, Haurat G, Goulas P (1987) Eur Patent Appl EP 240 423
Souppe J, Gisele H, Philippe G (1989) Fr Demande FR 2 621 325
Chocat P, Masse F, Souppe J (1989) Fr Demande FR 2 623 520
Donishi J, Yokozeki K (1989) Jpn Kokai Tokyo Koho JP 01 117 794
Schöpp W, SchÄfer A (1985) Fresenius Z Anal Chem 320: 285
Comtat M, Galy M, Goulas P, Souppe J (1988) Anal Chim Acta 208: 295
Aragozzini F, Maco E, Craveri R (1986) Appl Microbiol Biotechnol 24: 175
Brooks DW, Kellog RP, Cooper CS (1987) J Org Chem 52: 192
Nakamura K, Ushio K, Oka S, Ohno A, Yasni S (1984) Tetrahedron Lett 25: 3979
Fuganti C, Grasselli P (1985) Tetrahedron Lett 26: 101
Sih CJ (1987) US Patent Appl US 4 710 468
Sih CJ, Chen C (1984) Angew Chem 96: 556
Bare G, Jacques P, Hubert JB, Rikir R, Thonart P (1991) Appl Biochem Biotechnol 28/29: 445
Lindstedt G (1967) Biochemistry 6: 1271
Abbot M, Udenfried S (1974) In: Hayaishi O (ed) Molecular mechanisms of oxygen activation. Academic, New York, p 167
Hayaishi O, Nozaki M, Abbott MT (1981) Oxygenases: Dioxygenases. In: Boyer PD (ed) The enzymes, Academic, New York, vol 12, p 119
Lindstedt G, Lindstedt S, Nordin I (1977) Biochemistry 16: 2181
Kondo A, Blanchard JS, Englard S (1981) Arch Biochem Biophys 212: 338
Lindstedt G, Lindstedt S, Midtvedt T, Tofft M (1967) Biochemistry 6: 1262
Lindstedt G, Lindstedt S (1970) J Biol Chem 245: 4178
Blanchard JS, Englard S, Kondo A (1982) Arch Biochem Biophys 219: 327
Punekar NS, Wehbie RS, Lardy HA (1987) J Biol Chem 262: 6720
Wehbie RS, Punekar NS, Lardy HA (1988) Biochemistry 27: 2222
Lindstedt G, Lindstedt S, Tofft M (1970) Biochemistry 9: 4336
Lindstedt S, Nordin I (1984) Biochem J 223: 119
Lindblad B, Lindstedt G, Tofft M, Lindstedt S (1969) J Am Chem Soc 91: 4606
Englard S, Blanchard S, Midelfort CF (1985) Biochemistry 24: 1110
Holme E, Lindstedt S, Nordin I (1982) Biochem Biophys Res Commun 107: 518
Cavazza C (1982) Ger Offen DE 31 23 975
Kulla H, Lehky P (1985) Eur Patent Appl EP 0158194
Kulla H, Lehky P, Squaratti A (1986) Eur Patent Appl EP 0195 944
Kulla HG (1991) Chimia 45: 81
Nobile S, Deshusses J (1986) J Bacteriol 168: 780
Nobile S, Baccino D, Takagi T, Deshusses J (1988) J Bacteriol 170: 5236
Nobile S, Baccino D, Deshusses J (1988) FEBS Lett 233: 335
Nobile S, Deshusses J (1988) Biochimie 70: 1411
Nobile S, Deshusses J (1988) J Chromat 449: 331
Watanuki M (1990) Jpn Kokai Tokkyo Koho JP 02 119 786
Nakayama K, Miyama M (1990) Jpn Kokai Tokkyo Koho JP 02 69 189
Nakayama K, Miyama M (1990) Jpn Kokai Tokkyo Koho JP 02 69 188
Seim H, Ezold R, Kleber HP, Strack E (1980) Z Allg Mikrobiol 20: 591
Seim H, Löster H, Claus R, Kleber HP, Strack E (1982) FEMS Microbiol Lett 13: 201
Seim H, Löster H, Claus R, Kleber HP, Strack E (1982) Arch Microbiol 132: 91
Seim H, Löster H, Kleber HP (1982) Acta Biol Med Germ 41: 1009
Seim H, Kleber HP, Strack E (1979) Z Allg Mikrobiol 19: 753
Jung H, Jung K, Kleber HP (1989) Biochim Biophys Acta 1003: 270
Jung K, Jung H, Kleber HP (1987) J Basic Microbiol 27: 131
Seim H, Jung H, Löster H, Kleber HP (1985) Wiss Z Karl-Marx-Univ Leipzig, Math-Nat R 34: 287
Seim H, Löster H, Claus R, Kleber HP, Strack E (1983) DD 221 905
Seim H, Kleber HP (1988) Appl Microbiol Biotechnol 27: 538
Jung H, Kleber HP (1990) l-Carnitine synthesis by stereoselective hydration of crotonobetaine. In: Christiansen C, Munck L, Villadsen J (eds) 5th European Congress on Biotechnol 8–13 July 1990. Munksgaard Copenhagen, vol I, p 251
Jung H, Jung K, Kleber HP (1989) Eur Patent Appl EP 0 320 460
Yokozeki K, Takahashi S, Hirose Y, Kubota K (1988) Agric Biol Chem 52: 2415
Fukui S, Kawamura M, Akutsu S, Fukuda H (1984) Jpn Kokai Tokkyo Koho JP 61 67 499
Kawamura T, Iinuma S, Shinagawa S (1985) Jpn Kokai Tokkyo Koho JP 60 214 890
Kawamura M, Akutsu S, Fukuda H, Hata H, Morishita T, Kano K, Nishimori H (1986) Jpn Kokai Tokkyo Koho JP 61 234 788
Kawamura M, Akutsu S, Fukuda H, Hata H, Morishita T, Kano K, Nishimori H (1986) Jpn Kokai Tokkyo Koho JP 61 234 794
Kawamura M, Akutsu S, Fukuda H, Hata H, Morishita T, Kano K, Nishimori H (1986) Jpn Kokai Tokkyo Koho JP 61 271 995
Kawamura M, Akutsu S, Fukuda H, Hata H, Morishita T, Kano K, Nishimori H (1986) Jpn Kokai Tokkyo Koho JP 61 271 996
Whitesides GM, Wong CH (1985) Angew Chem 97: 617
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 1993 Springer-Verlag
About this chapter
Cite this chapter
Jung, H., Jung, K., Kleber, H.P. (1993). Synthesis of l-carnitine by microorganisms and isolated enzymes. In: Measurement and Control. Advances in Biochemical Engineering/Biotechnology, vol 50. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0007385
Download citation
DOI: https://doi.org/10.1007/BFb0007385
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-56536-9
Online ISBN: 978-3-540-47587-3
eBook Packages: Springer Book Archive